X-Ray, IR and 1H NMR Structural and Conformational Study of Highly Congested 2-Alkyl-1,3-diols and of 3-(1-Adamantyl)pentane-2,4-dione

Configuration of meso diols produced by LiAlH4 reduction of symmetric alpha-(1-adamantyl)-beta-diketones has been determined by X-ray diffraction. Large C-C distances and C-C-C angles have been measured for these strained molecules. Most of the studied 1,3-diols, both meso and d,1, exist in solution in conformations possessing intramolecular hydrogen bond. The conformations of two diols were also studied in the crystal phase.